Metal-Free Electrochemical Oxidative Difluoroethylation/Cyclization of Olefinic Amides To Construct Difluoroethylated Azaheterocycles

A new strategy of electrochemical oxidative difluoroethylation to generate difluoroethyl radical with sodium difluoroethylsulfinate (DFES-Na) has been reported for the first time. The method allows quick access to a variety of valuable difluoroethylated azaheterocycles including oxindoles and isoqui...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 88; no. 3; pp. 1875 - 1883
Main Authors Tian, Yunfei, Zheng, Luping, Wang, Zhiqiang, Li, Zejiang, Fu, Weijun
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 03.02.2023
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ALKENES
ACTIVATION
REAGENTS
INHIBITORS
CYCLIZATION
FLUOROALKYLATION
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Summary:A new strategy of electrochemical oxidative difluoroethylation to generate difluoroethyl radical with sodium difluoroethylsulfinate (DFES-Na) has been reported for the first time. The method allows quick access to a variety of valuable difluoroethylated azaheterocycles including oxindoles and isoquinoline-1,3-diones via radical tandem difluoroethylation/cyclization in moderate to good yields. The electrochemical cyclopropyldifluoromethylation of N-arylacrylamides also works well using this strategy. Moreover, radical capture and cyclic voltammetry (CV) experiments are also carried out to determine the proposed mechanism.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c02579